Assistant Controller

About the Role

We’re hiring an Assistant Controller to help build the foundation of finance and accounting operations at exacare ai as we scale. This is a highly operational and cross-functional role with ownership across billing, collections, month-end close, systems, and accounting operations.

You’ll partner closely with teams across Sales and Operations to improve processes, strengthen controls, and ensure financial data flows accurately across the business.

This is an opportunity to join early and help shape the future finance function at exacare ai. We’re looking for a high-agency, systems-minded operator who thrives in fast-paced environments and enjoys building scalable processes from the ground up.

You’ll work closely with finance leadership that has experience across Big 4 accounting and scaling accounting operations at high-growth technology companies, with meaningful exposure to systems, controls, revenue accounting, and process development.

This role is based in Toronto and requires in-office collaboration three days per week.

What You’ll Do

• Own core accounting operations including billing, collections, AP, reconciliations, and month-end close support
• Review customer contracts and ensure billing terms and account setup are accurately reflected in HubSpot and downstream financial systems
• Maintain and improve finance systems and data integrity across platforms including HubSpot, Brex, Rillet, and banking tools
• Own customer billing operations, collections workflows, AR reporting, and short-term cash collections forecasting
• Prepare monthly close schedules, reconciliations, workpapers, and operational reporting as accounting operations transition in-house
• Serve as a key point of contact for external auditors by preparing support, responding to requests, and helping drive audit readiness
• Support implementation of accounting policies, controls, and scalable operational workflows
• Partner cross-functionally with Sales, Customer Success, and Operations to improve processes and resolve operational issues
• Support broader finance, accounting, and operational initiatives as the company continues to scale

What You’ll Bring

• CPA designation required
• 3+ years of accounting experience, ideally with experience at a Big 4 accounting firm
• Strong understanding of accounting operations, month-end close, reconciliations, and core US GAAP principles
• Experience working with ERP, billing, CRM, and banking systems in a fast-paced environment
• Systems-oriented operator with experience building scalable processes and improving workflows
• Comfortable working independently, navigating ambiguity, and solving operational problems proactively
• Strong analytical, organizational, and communication skills with the ability to manage multiple priorities effectively
• High ownership mentality with a willingness to roll up your sleeves and execute in a startup environment
• Advanced Excel / Google Sheets skills and comfort working with large datasets and operational workflows

Benefits + Perks

• Competitive salary and equity in a high-growth startup
• Flexible PTO, take what you need
• Medical, dental, and vision coverage
• Great startup culture, including company off-sites
• Hybrid work out of our beautiful NYC Office
• High-achieving team, including ex-Amazon engineers and alumni of Bain, BCG, Goldman Sachs, and more
• The base salary range for this role is $135,000–$160,000 USD, depending on experience. Open to discussing outside this band for the right background or seniority level.

An insight into our Core Values

Only the best belong here

We are unapologetic about talent. This should be the best team you have ever been on. Protecting that standard is how we honor each other’s time, ambition, and craft.

We work even harder to keep our partners than we did to earn them initially

The work does not stop when a customer first onboards to our platform. It deepens over time. We partner with operators, listening and learning about real problems, and translate that into solutions that help them succeed in practice. We earn trust through consistent delivery.

We keep the patient downstream of every decision

At the end of the day, this is about the patient. We get there by deeply respecting and reflecting on our purpose: to develop software that aids teams in delivering better care.

Raise the bar on ownership

We grow because people here go beyond the minimum. We invest extra effort, care, and ownership into what we build.

The world is moving fast. We move faster.

This is a race. We work hard, we move early, and we stay ahead of problems and competitors. If we slow down, someone else will pass us.

Radical candor, zero politics

We say what’s true, early, and we keep communication direct and clean so the team can move.

Bring good vibes and win together

We win as a team. We bring energy, support each other, and make the workplace somewhere people are excited to show up.
If this sounds like you, we'd love to have a chat!